Cannabidiol (CBD) is a compound identified from cannabis that is pharmaceutically active. It is a phytocannabinoid and accounts for up to 40% of a cannabis extract. (Borgelt L M, et al., (2013), Pharmacotherapy, 33(2): 195-209; Aizpurua-Olaizola, Oier, et al., (2016), Journal of Natural Products, 79(2):324-331; Campos A C, et al., (2012), Philos. Trans. R. Soc. Lond. B Biol. Sci., 367(1607):3364-78). CBD is also found and isolated from other plants such as, e.g., hemp. CBD can also be produced and isolated by other methods of production including yeast manufacturing (see, WO2016/010827). CBD is presently used clinically in combination with (−)-trans-Δ9-tetrahydocannabinol (Δ9-THC) for treatment of neuropathic symptoms associated with multiple sclerosis (Morales et al., (2017) Front. Pharmacol. 8:1-18). CBD is also being investigated as a single agent for use as a neuroprotective, treatment of hypoxia-ischemia events, addiction and uses as an anxiolytic, antipsychotic, analgesic, anti-inflammatory, anti-asthmatic, anti-epileptic and anti-cancer agent (Fasinu et al., (2016) Pharmacotherapy 36(7):781-796; Fanelli et al., (2017) J. Pain Res. 10:1217-1224; Morales et al., (2017) Front. Pharmacol. 8:1-18; and Devinsky et al., (2017) N Engl J Med 376(21): 2011-20).
Cocrystals are crystalline molecular complexes of two or more non-volatile compounds bound together in a crystal lattice by non-ionic interactions. Pharmaceutical cocrystals are cocrystals of a therapeutic compound, e.g., an active pharmaceutical ingredient (API), and one or more non-volatile compound(s) (referred to herein as coformer). A coformer in a pharmaceutical cocrystal is typically a non-toxic pharmaceutically acceptable molecule, such as, for example, food additives, preservatives, pharmaceutical excipients, or other APIs. A cocrystal of an API is a distinct chemical composition of the API and coformer(s) and generally possesses distinct crystallographic and spectroscopic properties when compared to those of the API and coformer(s) individually. Crystallographic and spectroscopic properties of crystalline forms are typically measured by X-ray powder diffraction (XRPD) and single crystal X-ray crystallography, among other techniques. Cocrystals often also exhibit distinct thermal behavior. Thermal behavior is measured in the laboratory by such techniques as capillary melting point, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). As crystalline forms, cocrystals may possess more favorable solid state, physical, chemical, pharmaceutical and/or pharmacological properties or may be easier to process than known forms or formulations of the API. For example, a cocrystal may have different dissolution and/or solubility properties than the API, and can, therefore, be more effective in therapeutic delivery. A cocrystal may also affect other pharmaceutical parameters such as storage stability, compressibility and density (useful in formulation and product manufacturing), permeability, and hydrophilic or lipophilic character. New pharmaceutical compositions comprising a cocrystal of a given API, therefore, may have attractive or superior properties as compared to its natural state or existing drug formulations.